原位反应法制备菲基-螺-氧杂环聚合物及其光电性质

doi:10.7503/cjcu20150480

高等学校化学学报 ›› 2015, Vol. 36 ›› Issue (10): 2047.doi: 10.7503/cjcu20150480

原位反应法制备菲基-螺-氧杂环聚合物及其光电性质

王志明^1,², 王京¹, 侯雪¹, 张晓娟¹, 路萍²

1. 沈阳工业大学石油化工学院, 辽阳 111003
2. 吉林大学超分子结构与材料国家重点实验室, 长春 130012

收稿日期:2015-06-19 出版日期:2015-10-10 发布日期:2015-09-18
作者简介:联系人简介: 王志明, 男, 副教授, 主要从事光电功能材料研究. E-mail:wangzhm1983@163.com
基金资助:
国家自然科学基金(批准号: 51203091)和辽宁省博士启动基金(批准号: 20131084)资助

Preparation of a Polymer Containing Sprio-dioxolane Based on Phenanthrene Block via in situ Reaction and Its Photo-electro Properties^†

WANG Zhiming^1,^2,^*, WANG Jing¹, HOU Xue¹, ZHANG Xiaojuan¹, LU Ping²

1. School of Petrochemical Engineering, Shenyang University of Technology, Liaoyang 111003, China
2. State Key Laboratory of Supramolecular Structure and Materials, Jilin University, Changchun 130012, China

Received:2015-06-19 Online:2015-10-10 Published:2015-09-18
Contact: WANG Zhiming
Supported by:
† Supported by the National Science Foundation of China(No.51203091) and the Liaoning Province Doctor Startup Fund, China(No.20131084)

摘要/Abstract

摘要：

利用聚-(菲醌-alt-芴)(L-PPQF)中邻位羰基高效的反应活性, 将L-PPQF与乙二醇进行缩合反应, 制备了一类新型的含有菲基-螺-氧杂环的聚合物: 聚-(芴-alt-螺氧菲)(L-PPOF), 同时将L-PPQF的齐聚物二芴基-菲醌(L-DFPQ)与乙二醇反应生成二芴基-螺-氧-菲(L-DFPO). 对比L-DFPQ与L-DFPO的核磁、质谱和元素分析, 确定了螺-氧杂环结构的生成. L-PPQF和L-PPOF的核磁和红外光谱等分析结果也证实了L-PPOF同样具有螺-氧杂环结构. L-PPOF的光物理和电化学分析结果表明, 相对于L-PPQF和商业化产品聚芴(PF), 新生成的L-PPOF具有较高的溶液和固态效率以及合适的电子注入能级. 初步的电致发光器件测试结果证明, L-PPOF在电致发光功能性材料开发领域具有一定的价值.

关键词: 菲基-螺-氧杂环聚合物, 菲醌, 螺环, 氧杂环, 功能化, 光电性质

Abstract:

The reaction between carbonyl group in ketone or aldehyde and glycol is a class protection reaction in organic chemistry, and usually, the sprio-dioxolane structure was inserted to the original framework. In this work, the high-efficiency reaction was used between a kind of reactive polymer(L-PPQF) and glycol, because of the existence of reactive position in phenanthrenequinone block due to its ortho-carbonyl structure. A novel polymer containing sprio-dioxolane based on phenanthrene block was prepared by in situ reaction, and named L-PPOF. Collecting the results of NMR, MS and elemental analysis from the model oligomer(L-DFPQ) of L-PPQF and its product after in situ reaction, this new heterocyclic structure was confirmed. The polymer structure was also clear after chartering by the measurement in further such as NMR and FTIR. The data of photo-physical and electrochemistry show that, the newborn polymer containing sprio-dioxolane modified phenanthrene unit exhibited higher fluorescence quantum efficiency in solution and solid, more suitable electron-injection energy level than its matrix polymer L-PPQF or PF. The primary OLED performance implied the L-PPOF had good potential value.

Key words: Sprio-dioxolane polymer based on phenanthrene block, Phenanthrenequinone, Spiro, O-Containing heterocyclic, Functional, Photo-electro property

中图分类号:

O649

TrendMD:

王志明, 王京, 侯雪, 张晓娟, 路萍. 原位反应法制备菲基-螺-氧杂环聚合物及其光电性质. 高等学校化学学报, 2015, 36(10): 2047.

WANG Zhiming, WANG Jing, HOU Xue, ZHANG Xiaojuan, LU Ping. Preparation of a Polymer Containing Sprio-dioxolane Based on Phenanthrene Block via in situ Reaction and Its Photo-electro Properties^†. Chem. J. Chinese Universities, 2015, 36(10): 2047.

图/表 6

Synthesis routs of oligomers and polymers

Fig.1 1H NMR spectra of L-DFPQ(a) and L-DFPO(b)

Fig.2 Conformation of SDP from different views

Fig.3 1H NMR(A) and IR(B) spectra of L-PPQF(a) and L-PPOF(b) Insert of (B): TGA curve of L-PPOF.

Fig.4 Absorption-PL spectra of L-PPQF and L-PPOF(A) and CV curves of L-PPOF(a) and PF(b)(B)^Inset of (A): photo of L-PPQF and L-PPOF in THF under UV-light.

Fig.5 Luminous efficiency(A) and normalized EL intensity at 10 mA/cm2(B) of OLED performance of L-PPOF in Device A and Device B^Device A: ITO/PEDOT(40 nm)/L-PPOF(~50 nm)/CsF(1.5 nm)/Al(120 nm);device B: ITO/PEDOT(40 nm)/PVK(40 nm)/L-PPOF(~50 nm)/CsF(1.5nm)/Al(120 nm).

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原位反应法制备菲基-螺-氧杂环聚合物及其光电性质

Preparation of a Polymer Containing Sprio-dioxolane Based on Phenanthrene Block via in situ Reaction and Its Photo-electro Properties^†

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原位反应法制备菲基-螺-氧杂环聚合物及其光电性质

Preparation of a Polymer Containing Sprio-dioxolane Based on Phenanthrene Block via in situ Reaction and Its Photo-electro Properties†

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Preparation of a Polymer Containing Sprio-dioxolane Based on Phenanthrene Block via in situ Reaction and Its Photo-electro Properties^†